Say When
by delta-foxtrotwrites
Summary: She wanted the selfish part of her to be as determined as the part of her that loved him beyond reason. Literati oneshot set during 4x21


**Author's note: **It's been a long time since I've written anything, much less in third person, so I apologize if it's a bit of a mess to read. After doing a recent rewatch of Gilmore Girls I was stuck on this scene and being a big Lit shipper I finally gave in and started re-working it. What really convinced me to finally write this though was the song Say When (as it's named) by The Fray which I think fits their relationship really beautifully; the tone really encompasses all that is their ill-fated romance so if you have never heard the song I very, very highly recommend it. In saying that this is my revised version of the heart breaking lit scene in Last Week Fights, This Week Tights. I hope you like it.

**Disclaimer: **I do not own Gilmore Girls, the song Say When or anything else I may have mentioned that I could be sued for not clarifying I do not own. I do however own the Gilmore Girls box set and a penchant for writing instead of sleeping.

**Say When**

It was as if the very second he re-entered her life it became a romance novel of epic proportions. Though this chapter started with an indirect passive-aggressive defiance between her former lovers, it was no surprise that it would start off as a risky gamble, and then turn into something with higher stakes.

Jess was just as beautiful as he'd always been, though he hadn't had a haircut in what she had to guess was a few months now Rory thought it had the opposite effect, he looked tidier, less rugged than usual. He donned his signature biker jacket, and although she may have teased him about it time and again, she had to admit that she had always had a soft spot for his James Dean exterior. She had never been attracted to him because he was a 'bad boy' per se, more so than simply because she couldn't help herself. Nothing about her and Jess had ever made sense, they were polar opposites that seemed to have everything in common and she knew she loved him without a doubt, beyond any amount of reason that logic could provide. She had to; she had broken up with Dean because of Jess. She had missed her opportunity to be the small town girl that got married out of high school and lived in a town house with the safe, sweet guy that would never do wrong by her. She had chosen Jess, the reckless one, the one she was sure cared but didn't know how to show it, or handle it. Jess who had left her twice with no goodbyes, though perhaps the first time she was unreasonable to think she deserved one, she was sure they had at least been friends.

Jess was the boy she had skipped school to go see, missed her mother's graduation for; though she would never under any circumstances miss anything school related when Dean asked her to. She had given Jess almost anything he wanted, without him ever having to ask and in return he had told her he loved her, after disappearing to California and disappearing just as quickly again. In a way she could understand why he'd gone but it had never excused the fact that despite whatever they had been going through he had just left like it was so easy for him to do. He had seen her that morning and said nothing and she had found out from her mother, her mother who had told her so; her mother who had warned her over and over that Jess was the kind of boy that was only going to hurt her and get her in trouble. That was the worst part of it all, not that he had gone, just that she had been warned continuously that he would hurt her and she had decided to believe otherwise.

Sometimes she hated herself for it. Sometimes she wished she could naturally think the worst of people, especially when they had proven to be very capable of showing her the very worst versions of themselves. She wondered why she would always forgive him, and why she would always be happy to see him, even though she knew they didn't stand a chance. He never stayed anywhere with any degree of permanence and while he had said he loved her, she knew that the only consistent love in his life was the same as hers, books. That was the best part about them, the books, the notes he'd leave in her margins, the phrases he'd underline, the bits he'd read to her, the words she would tell him were her favorites and their shared dislike for book covers that had photos of people.

She hated that even after a year she would feel exactly the same standing in front of him as she did when they were together in high school. But things were definitely different now. She was in college, and from what she had gathered he had been living in New York which came as no surprise to her. He loved the city, she could see it in the way he had showed her around, in the way that he knew all the places in town she would like because they were so similar and he could get to each of these places without ever having to consult street signs or subway routes. She knew he could stay away for twenty years and still find his way around with ease and she was jealous of him for that. The fact that he came from New York seemed to add this maturity to him. He had grown up in a place where things happened, people got arrested, your neighbors kept you awake, there were concerts and big bookstores and art exhibitions. The only thing that sheltered him was the roof over his head. She was envious at even the slightest hint of a real scandal, even if it was just the person in the apartment upstairs getting noise control called on them. Stars Hollow didn't even have noise control.

Jess had always seemed worldly to her, informed, clued in to something she could only ever hope she'd be privy too and he was sure of himself. He had a certain demeanor he held himself with. Dean had come from Chicago, but he had always seemed like a small town boy to her. There was nothing about Dean that hinted at the fact that he had lived in a place that wasn't so quaint and close knit. He was polite and well spoken, he worked in the only grocer in town, and he had married only months after graduating. Dean had always been en-route to live the epitome of small town life.

Rory had lived in Connecticut her whole life and she still felt as if she had more life experience than Dean. Jess would always be leaps and bounds ahead of her though and it made her more curious about him. She knew what her motivations were and what she wanted out of life, because she had always been in the same place and she wanted to get out and explore the world, but Jess was hardly restrained, he could and did, do as he pleased, and she had to wonder what motivated him and what he wanted to do with his life. He had never let her in on any real life plan. He lived in the moment, planned nothing any further than two weeks ahead of time; he had no plan, just a divine puzzle to put together as he continued on his way.

She figured it must be fantastic not to feel obligated to anyone or anything, that it had to be wonderful to be able to just take off because you felt like it and not have to worry about informing every one of your plans. She would always envy the freedom he provided himself but she thought it must be lonely. She wondered if he ever missed her but she wouldn't ask. She didn't want to get her hopes up, and she doubted he would answer her questions anyway. His general evasiveness was still in fine form she noted, as he told her for a second time that he wanted to talk to her. He spoke to her directly, not-so-subtly letting Dean know that he wanted him to leave.

Rory had called Dean to pick her up after a misinterpreted invitation had landed her at one of the on campus pubs stuck with a group of wealthy frat boys who drank entirely too much and spoke of nothing she found she could even feign remote interest in. She had asked him if he wanted dinner in return, but she saw no reason for him to stay now. She had her car so she could drive back to Stars Hollow with her things in the trunk and come back tomorrow for the rest of the boxes she wouldn't be able to transport in her first trip. Jess showing up outside her dorm only further supported the fact that Dean had no reason being here when his wife was probably sitting at home waiting with his dinner on the table.

Rory frowned when he outright refused to leave when she asked him the first time and she could almost hear what he was thinking. 'As if I'm going to leave you alone with this guy,' though the look on Jess's face held no particular foreboding emotion towards Dean he knew that it was unlikely Jess was just stopping by to say hello and he refused to leave her unprotected but Rory gave him a pointed look and told him again.

Dean cleared his throat uncomfortably before turning down the hallway Jess had come from, heading back to his car and back to his wife. He was barely out the door before Rory pounced on Jess.

"Why won't you leave me alone? You won't go away!"

"Rory-"

"What do you want?"

She was really curious this time, to see what he could possibly have to say, how he would top his last appearance, because he always did. The first time he left after he crashed her car and she received a hairline fracture, the second time he left after she had really fallen for him, and had honestly thought that if he was the guy she spent the rest of her life with, she would be happy, and the third time was his infamous declaration, the I love you that had driven her completely crazy for weeks.

"I don't know. I just wanted to see you, talk to you, just…"

"What?"

All of a sudden she really noticed him, under that beautiful face of his and the tough exterior he had up but had vanished along with Dean. Suddenly he seemed vulnerable and small. For the first time he looked distinctly unsure, worried, his demeanor had completely changed, he wasn't exuding his usual confidence in that nonchalant way he did. It was as if he were completely off centre. He seemed nervous.

"Come with me" there was a quiet desperation in his voice, almost pleading for her to agree and she found herself scoffing at the idea before she could stop herself, questioning him again. He was insane, he couldn't seriously have just said that, suggested that to her.

He repeated the offer, sounding surer of himself this time, regaining a bit of his confidence when he noticed he'd caught her off guard.

In an instant he realized it felt like it always felt when he was around her. It felt like she wasn't close enough, but he didn't chance a step forward noting the look on her face of questioning, the confusion in her eyes. He didn't want to scare her, and he knew that she wasn't going to respond well to his seemingly irrational notion despite the fact that this was the most rational seeming thing to him.

"Where?" she questioned, and he supposed it was reasonable, he was always moving and she liked stability. He would take her anywhere she wanted, but he didn't say that.

"I don't know, away" he kept his answer vague, hoping she would interpret the less than forthcoming location as one that she was allowed to factor in her own suggestions for.

"Are you crazy?" her scowl deepened and she looked at him almost as if he were a stranger or speaking a language she couldn't comprehend.

"Probably. Do it, come with me, don't think about it" he urged.

By now Jess could feel the adrenaline pounding through his veins and he was beginning to understand why Rory was questioning him. She had no warning; he had just shown up, he was asking her to runaway with him. No wonder she was asking if he was crazy and maybe he was for asking her, but he had to. He had to try. He was so sure that this could be what they needed; this crazy notion could break them away from the undesirable reality that kept her from him.

"I can't do that" she told him, turning around and pushing her door open. He followed her in, finding what he had to assume was the common room of her dorm, filled with towers of boxed belongings.

"You don't think you can do it, but you can, you can do whatever you want" He insisted, remarking that this surely was a perfect coincidence.

"It's not what I want!"

Her voice raised a little and her tone sounded just a little frenzied. He knew he must be driving her insane, but he couldn't find it within himself to give up. He had to try to convince her that this was the best for them, that they could finally be together and he would be better this time, infinitely. He knew there was no more room for him to screw up again.

"It is, I know you."

"You don't know me" Rory reprimanded him and it felt like a bucket of cold water had been thrown in his face. How could she even suggest he didn't know her? She was all he knew, all he wanted to know. She was and had been the most important thing, the first and foremost matter on his mind. Regardless of the time they had spent apart he had spent all of his time without her knowing who she was and who she would be, and wondering just how she was now. She was wrong but he didn't argue the point with her because he knew it was no use. He was running out of time, and out of chances, he could feel her slipping right through his fingers.

"No, look, we'll go to New York, we'll work, we'll live together, we'll be together, it's what I want, it's what you want too!" Jess persisted, hoping against hope that if he provided the basics, an outline of structure that she could expect it might stop her from refusing him.

"No!"

"Look, I want to be with you, but not here, not this place, not Stars Hollow!"

He said the name of her hometown in disdain and it only reinforced with her the reality that there wasn't a lot of hope for them. "There's nothing to start" She pressed, adamant, her tone begging in exasperation for him to listen to her and hear what she was saying.

"You're packed, your stuff is in boxes, its perfect, you're ready and I'm ready, I'm ready for this, you can count on me now, I know you couldn't count on me before but you can now, you can!"

His words broke Rory's heart. He sounded devastatingly sincere and it showed in his anguished expression but she couldn't do this with him, not now. She didn't know if she could ever do this with him. He was asking her to give up everything, Yale, her hometown, her mother, and her friends. They wouldn't have much money; she wouldn't be able to visit as often as she would need to in order to keep sane. It was sad that he was finally willing to make the commitment she had hoped he would make to her so long ago, and yet the offer was so out of the question. There was no way she could accept.

"No."

She spat the word out, knowing that in his desperate attempt to convince her; this protest wasn't going to deter him.

Jess stepped forward, taking her hands into his and Rory gave him a bit of herself upon contact, regardless of her resolve. She couldn't help herself, couldn't stop herself from wanting to fall into his touch, for wanting his hands to move somewhere else, her waist, her back, her neck, anywhere else. She just wanted him to surround her. She wanted to breathe him in and revel in that scent that was so uniquely Jess. She wanted to feel that same sense of liveliness she felt when she was with him in spite of the fact that she was refusing to go with him. She wanted the selfish part of her to be as determined as the part of her that loved him beyond reason so she could say yes. He'd put her boxes in his car, and she'd read the book he had stashed in the glove box while they drove through to New York and it would be perfect. They'd be complacent and satisfied, having finally found a resolution. But she couldn't give up her life for him, this wasn't the right solution for them. She refused to be that girl. She refused to be the teenage girl that threw her life away for a guy who had never been able to prove she could count on him. She wouldn't get swept up in what could be her own personal love story if it meant losing her livelihood. She had worked hard to get into Yale, she had friends, her family was close by, she couldn't give that up for him, she didn't want to.

"Look, you know we're meant to be together. I knew it the first time I saw you two years ago, and you know it too, I know you do."

"Jess, I, no, I can't."

"Don't say no to make me stop talking or make me go away, only say no if you really don't want to be with me."

Rory said nothing. She couldn't say anything. There was nothing she could say that would be anything besides a partial truth or a partial lie. She did want to be with him, of course she did but not like this. She didn't want to runaway with him no matter how romantic the notion seemed to be. There wasn't much romantic about this, it was selfish and impossible. She couldn't and wouldn't do it.

Jess ghosted his hands up her palms and gently encircled her wrists, pulling her a few short steps forward. He fixed his gaze on her and she could see the determination in his eyes as he began to talk again. "I meant it, the last time we saw each other, I meant what I said." The infamous 'I love you' she thought, she hadn't needed him to remind her of that. She knew he meant it the same way she knew everything about him that she did. It was instinctual, uncontrollable and involuntary the way they felt about one another, knew one another. She knew he'd told her simply because he had to, not because he had wanted her to know and she knew this because she had watched him run away from her right after he said it and drive away. He didn't wait for a reaction, to see the look on her face, or the small smile that snuck onto her lips before she regained her composure and frowned as she stared after his car that was city bound.

Rory nodded, "I know you did" she replied, her fingers slipping under the cuffs of his sleeves to run over the smooth skin of his wrists. It was almost scary really, the weight those words had carried when he had said them to her, they had never seemed so significant, so completely unexpected and yet unsurprising. It didn't come as a shock to her that he felt that way about her. She had been hanging out with Lane one afternoon when she had pointed it out.

'He loves you, you know that right?' she had said after Jess had run into them on his way back to the diner from the Doose's rubbish bins. Rory could remember the scene vividly because it was the first time she had realized. As soon as Lane had said that to her she had looked at his figure getting further away in the distance and it had dawned on her as if it were the simplest thing in the world. 'Yeah, he does' she had said and in that moment it was as if her entire life snapped into focus and for the briefest of moments life offered her one small glimpse of a perfect clarity.

It surprised Rory how quickly their high tensioned situation had diffused and all it had taken was the small contact between them to do it. It had always been and probably would always be that way between them. They both became high strung and defiant and then gradually fell into companionable silence. Just like their common love in books it was one of the finer parts of their relationship, a part that was uniquely them. They found every understanding in silence; they didn't throw hateful words at one another, or even lavish each other in compliments and flattery. They could spend hours in silence and it would never be considered wasted time. With Jess Rory only ever needed to just be. She knew everything about him from the way he acted versus the things he said. Their banter, though it was always easy going and never lulled in awkward moments with either of them searching for the right words spoke in hushed tones in comparison to the way they acted around one another. Even now the simple gesture of holding one another's wrists was more intimate to them than any spoken 'I love you.'

"You love it here don't you? The classes, the lectures, the libraries, all of it" Jess spoke up after a few moments.

Rory looked around her box filled room, out into the empty courtyard outside and half smiled, "yes, I really do. If you'd come earlier I would have shown you around. I think you'd like it here."

Jess nodded but said nothing and Rory could tell he was biting his tongue on something but she didn't press him because he wasn't pressing her.

"I don't know how many times I've walked around this campus and wished I could share it with you, you're the only person in the world who would love it here the same way I do" she admitted, tugging his wrists without a thought to bring him closer. She breathed him in like she had wanted to and let the breath out in a sigh.

"So share it with me, right now, show me around. Share your new world with me." His voice was low and dangerous, enticing and everything she remembered it to be. She felt like the schoolgirl she had been when he'd first come to town and she had been intrigued by him despite her best efforts to keep all her interest focused on Dean. It was an impossible task, not to be intrigued by Jess. She wanted to know him, this person who was so much like her but so very, very different. She couldn't help but begin leading him out of her room and into the cool air of the courtyard, nostalgic for the stolen moments they had shared when she had been with Dean.

She had known, even then as every moment was occurring that it shouldn't have been. She always knew that Dean would be upset with her for spending time with Jess, but it didn't stop her and it only encouraged him. He had done everything in his power to steal moments from Dean and he had succeeded near effortlessly. He was the guy who had bought enough money to the bid-a-basket lunch, the one who read books not because she wanted him to but because he would enjoy reading them, and talking to her about them, he brought her care packages when she was home alone and swindled an invite out of her when Dean had failed and Paris had only managed to attain an hour of her time. Jess was nothing if not an exceptional thief. He had stolen her too many times to count.

Rory led him around the dark and empty campus; their wrists now free from the others hands instead finding themselves tied to one another simply by the gravity that kept them within centimeters of each other. He listened to her avidly as if every word might be the last one he heard her speak as she told him anecdotes of certain memories for certain places and facts about different buildings she pointed out to him. She was candid and beautiful in this moment as she shared her new world with him in a way he knew she'd never shared it with anyone. He knew he was only getting quarter of the tour she would have taken him on in the daylight hours but he was happy that even for half an hour they could wander around and just spend time together and it felt just as natural as it always had.

This wasn't how it was supposed to have been though and he knew that. He was supposed to have gotten this tour barely days into her first semester, where everything was new and she didn't have as many stories. But he would have reveled in hearing her first impressions and she would have reveled in getting to experience some of them with him at her side. He'd had a plan. He had never told her about it, but he had thought about what they would do when she was at college. He was going to drive up on Friday afternoons to spend the afternoon with her. He would read while she would study and then he would drive her home for the weekend so she could spend time with her mom. He would drop her off at her grandparents' house for their Friday night dinners and put her weekend stuff and laundry into Lorelai's car and he would see her in the morning at Luke's where he'd give her breakfast and she'd kiss him over the counter briefly. She'd spend the weekend with her mom and he'd drive her back on Sunday night with her clean laundry and her new books, they'd say goodbye after they watched a movie in her dormitory common room and he tolerated her roommates and he'd drive back to Stars Hollow and work for Luke and work at Wal-Mart until he found something better. That was how he had wanted it to be. He had looked forward to driving those 22.8 miles the first time to surprise her on her second day. He had been sure that was as long as he'd last the first time round.

It would have gotten easier in time not to see her everyday and he would have gotten better at missing her without immediately remedying the situation. They would have had their Friday afternoons and Sunday nights and the occasional spontaneous visit during the week that he knew would have been intentional and she would have pretended to be surprised by to spare his ego, at least the first few weeks. But he'd let everything pile up on him. He'd allowed himself to get overwhelmed and his fight or flight mentality had kicked in and he had fled town immediately. He hadn't said a word to her about it. He couldn't even comprehend the idea of telling her, because he had seen what it had done to her last time and what she had sacrificed to see him. He figured that if he severed the tie like that, left without telling her that she would just hate him, she wouldn't seek him out. It had been a good plan, he had thought. That was until he had called on her graduation day and she had told him that she could have loved him.

He had wrestled with that information for months before he decided to let it be. He knew he was no good for her, that he only ever brought her down. He wasn't boyfriend material, he was incapable of maintaining good relationships, and the pretense in which they'd met in the first place was a testament to that. Hell, before Rory he had never given a damn about any girl before in his life. He knew he was a jerk, a jerk who had never deserved her because she'd always been good, she was nice, polite, with good grades and a good reputation and she cared about the people around her. He had no idea what she saw in him, though he did understand that in comparison to Dean his and Rory's compatibility sky rocketed and there had always been chemistry between them. Other than that though he was dumbfounded.

It was easy to leave things between them as were when he was only left with his self deprecating thoughts to deter him from approaching her; it was when he saw her that he knew he was a goner. He'd tried to avoid her, even though he knew only the most marginal part of him didn't want to see her, he'd gone in the opposite direction every time they crossed paths but he could only leave her alone for so long. He couldn't help himself; if he could have he wouldn't have been on the campus in the first place.

Now that he was here though, and he had said all that he had, and Rory had shared this part of her life with him he realized how selfish it was of him to ask her to leave it behind, especially for him. If he could guarantee her something, then perhaps it might have been a different story, but there was little he could promise her and even less that he could offer her. All he could give her was himself, it was all he had and he knew that she deserved better, and he wished he could give her that instead. Fate was playing such a cruel joke on the both of them, making them so ill-fated. The timing was never right, he had to believe that, that it wasn't that they weren't right for each other, just that they never aligned correctly with time, they were always in different places.

When they arrived outside her residence hall they both knew that something had changed dramatically between them during their brief tour.

"I should go" he told her, taking a guess at the time.

"Oh…" She trailed off, looking down briefly before looking back up at him with a weak smile on her face, "Okay, I mean, I should probably start heading back to Stars Hollow anyway."

A part of her was disappointed. Jess had stormed in here with his grand gesture and now he was just leaving, but she knew it wasn't because he'd changed his mind about her, she could tell that much from the way his gaze lingered on her before he turned and looked over at his car, turning back just as quickly to really memorize every detail of her. He knew this picture had to last, he didn't know how long it would be before he saw her again but there was no doubt in his mind that he would.

His face was sheepish for a moment as he rubbed the back of his neck, "I'm sorry, I just wanted you to know that."

"Sorry? For what?" she asked, her bright blue eyes mirroring her questioning.

"I shouldn't have laid all that on you" he explained. "I shouldn't have just left like that; I shouldn't have run away from you. I should have handled things different, especially tonight."

Rory nodded her head, more in understanding than agreement. He'd never handled things spectacularly, that was true, but she had never expected anything more from him and she would never change that part about him.

"Anyway…" He tossed his head in the direction of his car, slowly beginning to walk away from her. "You look good" He added, flashing her his crooked smile. He saluted her before he turned around and his steps picked up speed.

"Jess!" Rory called out his name across the empty courtyard, worried that he had already gotten too far and he might not hear her.

Jess turned around and looked at her expectantly.

"It wouldn't matter if I went with you tonight or not" she announced, taking a calming breathe before she smiled at him, "I'm still going to be in love with you anyway."

* * *

Thank you for reading, if you would like to show your appreciation there is an option to leave a review ;p


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